Total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor

Mañas, Carles Giró; Paddock, Victoria L.; Bochet, Christian; Spivey, Alan Christopher; White, Andrew J. P.; Mann, Inderjit; Von Oppolzer, Wolfgang

doi:10.1021/ja910184j

Scientific article

English

Total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor

ContributorsMañas, Carles Giró; Paddock, Victoria L.; Bochet, Christian; Spivey, Alan Christopher; White, Andrew J. P.; Mann, Inderjit; Von Oppolzer, Wolfgang

Published inJournal of the American Chemical Society, vol. 132, no. 14, p. 5176-5178

Publication date2010

Abstract

A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

MAÑAS, Carles Giró et al. Total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor. In: Journal of the American Chemical Society, 2010, vol. 132, n° 14, p. 5176–5178. doi: 10.1021/ja910184j

Article (Published version)

Identifiers

PID : unige:6002
DOI : 10.1021/ja910184j

Journal ISSN0002-7863

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Total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor

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